5,5-Dibromo-4-chloro-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one → 4-chloro-5H,6H,7H-pyrrolo[2,3-d]pyrimidin-6-one

HRID 641368

Reaktionsgleichung

Reaktionsgleichung von HRID 641368
Br[C:2]1(Br)[C:10]2[C:9]([Cl:11])=[N:8][CH:7]=[N:6][C:5]=2[NH:4][C:3]1=[O:12]>C1COCC1.[Cl-].[NH4+].[Zn]>[Cl:11][C:9]1[C:10]2[CH2:2][C:3](=[O:12])[NH:4][C:5]=2[N:6]=[CH:7][N:8]=1

Komponenten

5

Edukt 1

HCID 223909585,5-Dibromo-4-chloro-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one

Produkt 1

HCID 120958704-chloro-5H,6H,7H-pyrrolo[2,3-d]pyrimidin-6-one

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23994ZincKatalysatorHCID 8028TetrahydrofuranLösungsmittelHCID 25517Ammonium ChlorideLösungsmittel

Versuchsvorschrift

Zinc (6.05 g, 92.56 mmol) was added to a solution of 5,5-dibromo-4-chloro-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one from Step A (3.03 g, 9.26 mmol) in THF (20 mL) and saturated aqueous ammonium chloride (5 mL). After 3 h, the reaction mixture was concentrated in vacuo and purified by HPLC using a reversed phase C18 column and eluting with a gradient of H2O:CH3CN:CF3CO2H-90:10:0.1 to 5:95:0.1. Lyophilization provided the title compound. MS: 71/Z=170 (M+1).

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. custompurified by HPLC
  3. washeluting with a gradient of H2O

Quellen und Nachweise

ORD-Eintrag
ord-78aa12f10954491ca32112b36f335302
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07696192B2

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